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Triethylamine → 1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea

HRID 1979482
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HRID 1979482 반응식
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.[C:25]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:35])[C:26]1[CH:34]=[CH:33][CH:32]=[C:28](C([O-])=O)[CH:27]=1.C(C(C[N:51]1[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[N:55]([CH:62]2[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]2)[CH2:54][CH:53]([NH2:68])[C:52]1=[O:69])=O)(C)(C)C>O1CCCC1>[O:69]=[C:52]1[NH:51][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[N:55]([CH:62]2[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67]2)[CH2:54][CH:53]1[NH:68][C:23]([NH:20][C:28]1[CH:32]=[CH:33][CH:34]=[C:26]([C:25]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:35])[CH:27]=1)=[O:8]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 154908351-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineHCID 184201251,3-Benzenedicarboxylic acid, mono(phenylmethyl) ester

생성물 1

HCID 212018741-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea
수율 91.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

Diphenylphosphoryl azide (938 mg) and triethylamine (354 mg) were added to a solution of monobenzyl isophthalate (874 mg) in anhydrous tetrahydrofuran (30 ml), the mixture was stirred at 100° C. for one hour and 30 minutes. The resultant mixture was allowed to cool, 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (680 mg) was added thereto, the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3), to thereby obtain 890 mg of the title compound.

후처리

  1. temperatureto cool
  2. stirringthe mixture was stirred at room temperature for one hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

출처 및 근거

ORD 기록
ord-d3a24068c3ab4c7899dd0dd5280dceac
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06239131B1

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